Builder first.Executive second.

Rachel Wolan

Chief Product Officer at Webflow. Formerly GM at Dropbox. I lead by building.

I write about AI products, agentic systems, and what it looks like when executives pick up the tools their teams use. The fastest way to lead through the AI transition is to build with it yourself.

Now
CPO @ Webflow
Based
San Francisco
Reach
LinkedInX
Rachel Wolan, Chief Product Officer at Webflow
FEATURED PROJECT // ONGOING

The AI-Native Exec Toolkit.

A complete guide to becoming an AI-native leader. Personal AI tools, prototyping playbooks, builder day frameworks, and the org-evolution patterns that follow when executives start shipping their own software.

Open the toolkit →
01All featured →
Featured / Now

How I AI with Claire Vo

A long-form conversation with Claire Vo on what it actually looks like to use AI day to day as a CPO. Workflows, agents, and the habits that compound.

Watch on YouTube / Podcast →
02

Writing.

All writing →
03

Investments.

BountiAI-powered prospecting and outreach for B2B sales teams.ExitedMetronomeUsage-based billing infrastructure for modern SaaS.Acq.Stripe~$1BSpeakeasySDK and agent-tooling layer for APIs.ExitedPreparedAI-assisted communication platform for 911 emergency response centers.Acq.Axon~$800MFermatAI-native canvas for creative and design work.BobyardAI construction takeoffs and estimation for contractors.CrewAIMulti-agent workflow orchestration framework.GrowthXCommunity and AI tooling for growth marketers.You.comAI-first search and productivity assistant.AndoAI assistant for everyday operations work.

Get in touch.

Available for speaking, podcasts, panels, and Webflow job referrals. Reach out on LinkedIn or X.